Angewandte Chemie International Edition · 2008 · 126 citations · 22 references
Natural SciencesChemistryMedicinal ChemistryDrug DesignOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisRetrosynthetic AnalysisStereochemical OptimizationAsymmetric Heterocycle SynthesisChemical Synthesis Of AnaloguesChemo-selectivityHeterocycle FunctionalizationMedicinal Chemistry Applications
Tackling the supply problem: A short and efficient synthesis of (−)-oseltamivir has been developed which requires eight steps from commercially available starting material and proceeds with an overall yield of 30 %. Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA, see scheme) as well as a chemo-, regio-, and stereoselective aziridination reaction. Phth=phthaloyl.
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Choung U. Kim, Willard Lew, Matthew A. Williams et al. · Journal of the American Chemical Society · 1997 · 1.1K citations